Sissy Shemale Videos » 33

KeekAss

BRAZILIAN TRANSEXUAL HOOKER ANDREA ROJO

Categories: amateur, anal, brazilian, hd, interracial, ladyboy, latina, lingerie, mexican, pov

aShemaleTube

Cute Tgirl with a Big Bulge and Puffy Nipples Milks her Tits and Slap them so Hard

Categories: amateur, ass, bathroom, blonde, close up, curvy, cute, femboy, fishnet, homevideo

aShemaleTube

Fucking Trans Kelsey Masters Raw Hardcore - Compilation 2

Categories: amateur, american, beauty, big ass, blowjob, compilation, couple, crossdressing, femboy, fishnet

KeekAss

Your Naughty Trans Neighbor Sends You And Waits For You To Shag Her - Uber-cute Tgirl Neighbor

Categories: amateur, crossdressing, cute, femboy, fetish, handjob, hd, ladyboy, masturbation, naughty

KeekAss

Hasty food sissy

Categories: cosplay, crossdressing, cute, femboy, fetish, food, handjob, hd, masturbation, redhead

aShemaleTube

gas station slutwalk bottomless

Categories: amateur, big ass, crossdressing, femboy, fetish, hd, ladyboy, latex, lingerie, outdoor

aShemaleTube

I love being a white sissy bitch slut whore for all of my irresistible BIG BLACK DADDIES

Categories: big ass, bitch, black, blonde, crossdressing, daddies, femboy, fetish, hd, interracial

aShemaleTube

Sissy strips to lingerie, twirls and smokes

Categories: corset, crossdressing, fetish, hd, lingerie, sissy, slut, stockings, tgirl

TrannyOne

Shemale and sissy sluts pounded by strangers

Categories: anal, anus, ass, crossdressing, gloryhole, hd, orgy, sissy, slut, stranger

aShemaleTube

Asian sissy femboy having sissygasm

Categories: amateur, asian, crossdressing, cumshot, femboy, fetish, futanari, hd, sissy, small cock

aShemaleTube

Short Haired Girls

Categories: amateur, anal, blowjob, compilation, femboy, hd, ladyboy, pov, short hair, sissy

aShemaleTube

tall mistress in leather

Categories: barebacking, big cock, big tits, blowjob, domination, fetish, hd, ladyboy, leather, mistress

aShemaleTube

I had to show him my secret ASSet...

Categories: amateur, anal, barebacking, big black cock, blowjob, cage, domination, femboy, hd, model

KeekAss

Wonderful Tranny Rileydix is taunting and has a Fine Arse

Categories: amateur, ass, balls, beauty, big ass, blonde, crossdressing, cute, dirty talk, doggystyle

aShemaleTube

Nerd trap sissy wanks her shecock

Categories: amateur, homevideo, masturbation, nerdy, sissy, solo, teen (18+)

TrannyOne

fuckmachine ass fucking pig

Categories: amateur, anal, anus, ass, assfucking, bdsm, booty, crossdressing, dildo, domination

aShemaleTube

Beautiful trans girl plays with her MASSIVE lady stick and cums !

Categories: amateur, beauty, big ass, big cock, big tits, creampie, cum, homevideo, masturbation, sissy

aShemaleTube

Livi

Categories: anal, barebacking, big tits, blowjob, cum in mouth, cumshot, femboy, hd, homevideo, latina

aShemaleTube

Sissy V stretches her hole

Categories: amateur, anal, big ass, ebony, hd, homevideo, lingerie, masturbation, model, sissy

aShemaleTube

Sensual Bella erotic masturbation 🍆💦💋

Categories: artistic, big cock, cumshot, erotic, femboy, hd, homevideo, latina, masturbation, music

aShemaleTube

CdTina’s turn

Categories: amateur, big cock, crossdressing, cumshot, fetish, hd, long nails, masturbation, mature, sissy

JizzBunker

Toomanypeaches adorable white sissy

Categories: adorable, babe, beauty, blonde, masturbation, sissy, small tits, solo, teen (18+), white

aShemaleTube

the fagot sissy slut shows up in the park

Categories: amateur, hd, park, sissy, slut

TrannyOne

Hardcore deepthroating facefuck a blindfold sissy slave

Categories: amateur, bdsm, big cock, blindfolded, blowjob, crossdressing, deep throat, dick, domination, european

aShemaleTube

4 differnet tights

Categories: amateur, big cock, big tits, crossdressing, femboy, fetish, hd, outdoor, sissy, solo

aShemaleTube

grosse salope gay

Categories: amateur, anal, gay, hd, mature, outdoor, sissy

aShemaleTube

BDSM style double dildo anal fuck

Categories: anal, asian, bdsm, chinese, cumshot, dildo, femboy, fetish, hd, ladyboy

aShemaleTube

Hung blonde Princess needs 2 hands 🍆💋

Categories: balls, big cock, blonde, edging, european, femboy, hd, homevideo, legs, masturbation

aShemaleTube

Indian Sissy waiting on her date

Categories: hd, hotel, indian, interracial, motel, sissy, slut

aShemaleTube

Rubbing my girly cock to strangers

Categories: amateur, crossdressing, dick, femboy, hd, homevideo, lingerie, masturbation, rubbing, sissy

KeekAss

Selenas XXL Rump Anal Invasion boinking Marathon Pin trio

Categories: amateur, anal, anal toying, ass, big ass, crossdressing, dildo, fucking machine, hd, ladyboy

TrannyOne

Sissy Bitch Chastity Caged ruined orgasm

Categories: amateur, bdsm, bitch, cage, creampie, crossdressing, cum, cum in mouth, cum swallowing, dick

VideoSection

Sissy Rozebell loves indulging in that ebony cock, can't get enough of it

Categories: amateur, beauty, big black cock, cosplay, crossdressing, dick, ebony, femboy, sissy

aShemaleTube

The Tiniest Dick - Sissy

Categories: anal, big ass, dick, dildo, fucking machine, masturbation, mature, pussy, sissy, slut

KeekAss

Beautiful Rebecca Vanguard is railed by shemale sissy Bambi Bliss

Categories: babe, beauty, blowjob, brunette, creampie, deep throat, fetish, licking, missionary, perky

Pornstars: Bambi Bliss

aShemaleTube

Goth Princess Whore Tiffany Minx - Male Voice Over Story Slow Motion Blow Job

Categories: amateur, blowjob, cage, crossdressing, cumshot, domination, femboy, goth, pornstar, sissy

Pornstars: Tiffany Mynx

aShemaleTube

Julia X Sweet Release

Categories: big cock, cumshot, femboy, hd, high heels, homevideo, lingerie, masturbation, pornstar, sissy

Pornstars: Sweet Julia

aShemaleTube

Asian Femboy lustful shower

Categories: amateur, asian, blonde, cumshot, femboy, hd, homevideo, ladyboy, masturbation, model

Pornstars: Viper

TrannyOne

Crossdresser takes huge cock

Categories: amateur, anal, anus, ass, big cock, blowjob, couple, crossdressing, cum, dick

aShemaleTube

Jenna Bella

Categories: ass, big cock, crossdressing, femboy, hd, lingerie, masturbation, sissy, small cock, small tits

aShemaleTube

Sissy Stacie Stars used by Daddy

Categories: amateur, anal, crossdressing, daddies, femboy, hd, sissy

TrannyOne

sissy wants that sheamle dick

Categories: big ass, big cock, big tits, creampie, cumshot, dick, gay, hd, homevideo, sissy

aShemaleTube

Sissy Maid Krissy Small Penis Humiliation - female voice over SPH with chastity feminization

Categories: amateur, anal, blowjob, cage, crossdressing, dick, femboy, feminization, fetish, hd

KeekAss

super-fucking-hot t-model cougar toying with enormous fucktoys and jizz

Categories: amateur, anal, anal toying, big ass, cougar, crossdressing, hd, jizz, mature, milf

HClips

Cucumber In My Sissy Ass

Categories: amateur, ass, big ass, brunette, cucumber, fetish, lingerie, sissy, solo, stockings

TrannyOne

Proving To Him That I'm Really A Girl - Sissy Caption Story

Categories: big cock, blonde, blowjob, creampie, cum, deep throat, dick, doggystyle, futanari, hd

UPornia

Sissy Oksana Riding A Monster Dildo Closeup

Categories: amateur, close up, dildo, hd, lingerie, riding, sissy, solo, stockings, toys

aShemaleTube

Slapping my sissy worthless balls makes me sissygasm

Categories: balls, femboy, fetish, lingerie, sissy, solo

KeekAss

My butt was pleading for beef whistle to poke it in this zero 2 bondage suit

Categories: anal, ass, big cock, blonde, blowjob, bondage, catsuit, cosplay, cute, femboy

KeekAss

Sissy in micro bathing suit gulping 1l of beer throughout buttfuck and then shoving it out

Categories: amateur, anal, assfucking, bathroom, bikini, blonde, crossdressing, enema, extreme, femboy

aShemaleTube

EveValentine Cums

Categories: blonde, cum, cumshot, femboy, glasses, homevideo, lingerie, masturbation, sissy, small tits

KeekAss

Mind-Blowing Sissy Model

Categories: brunette, compilation, crossdressing, danish, glamour, hd, lesbian, lingerie, mature, model

KeekAss

Sissy Maid - Anguish & Enjoyment Restrain Bondage

Categories: amateur, bdsm, beauty, big cock, bondage, crossdressing, domination, fetish, latex, lingerie

aShemaleTube

Sissy has kinky edge session

Categories: cage, crossdressing, dick, edging, hd, kinky, ladyboy, sissy, solo, webcam

UPornia

Sissy Slut & Bbc Booty Bumpin Magic

Categories: amateur, big black cock, big cock, booty, hd, interracial, sissy, slut, stockings, teen (18+)

aShemaleTube

Swiss femboy sissy gets fucked hard bareback by a TS and breeding

Categories: barebacking, boy, femboy, hardcore, hd, sissy, slut, swiss, transsexual

KeekAss

Railing an meaty fake penis with my cock-squeezing bum made me jizm

Categories: anal, big ass, big cock, boy, cum, cumshot, dick, dildo, femboy, gay

KeekAss

Solo Masturbating Tranny Chick Jacks Off

Categories: amateur, beauty, big tits, blonde, deep throat, femboy, homevideo, jerking, kissing, masturbation

aShemaleTube

White sissy fucked by BBC who fills my mouth with cum - Laylacross

Categories: amateur, anal, big black cock, big cock, cum, cum in mouth, deep throat, french, hardcore, hd

TrannyOne

sissysubkrystal Solo prostate milking handsfree cum

Categories: american, anal, anus, ass, big cock, booty, cum, dick, domination, hd

UPornia

Goth Sissy Mimsy Taking Anal Dildo And Getting Self Facial 9 Min

Categories: amateur, anal toying, facial, goth, sissy, solo, stockings, toys, webcam

aShemaleTube

Cute Naked Sissy Dildo Fuck and Dirty Talk

Categories: asian, crossdressing, cute, dildo, dirty talk, femboy, fetish, hd, homevideo, masturbation

Pornstars: Viper

aShemaleTube

ROUGHNECK vs Faggyboi: Stepdaddy Again

Categories: big black cock, blowjob, crossdressing, domination, femboy, gay, hd, sissy

aShemaleTube

Goth Princess Whore Tiffany Minx - Blowjob In Triplicate

Categories: amateur, big cock, blowjob, crossdressing, cum in mouth, cumshot, femboy, goth, hd, pornstar

Pornstars: Tiffany Mynx

KeekAss

Purple Hair Transbabe Shows Off Body And Jerks

Categories: amateur, american, beauty, blonde, brazilian, crossdressing, doggystyle, ebony, femboy, homevideo

TrannyOne

Sissy Public Masturbation on the Balcony CutePinkUnicor

Categories: balcony, crossdressing, hd, masturbation, public, sissy, transvestite

aShemaleTube

.riding

Categories: amateur, anal, femboy, hd, homevideo, lingerie, sissy, solo, stockings

aShemaleTube

Joselynne Crossdresser Using Buttplug Tail In My Ass

Categories: amateur, anal, anal toying, ass, big ass, buttplug, crossdressing, femboy, high heels, latina

XXXDan

Your sissy whore in boots

Categories: amateur, boots, dildo, european, italian, mature, pantyhose, sissy, slut, solo

aShemaleTube

Caged femboy trains ass & cums💦

Categories: anal, ass, big cock, buttplug, cum, cumshot, curly haired, dildo, femboy, hd

aShemaleTube

Exposed Sissy Bitch Tiffany Minx – Blowjob - Sissy Commentary Filthy Dirty Talk

Categories: bitch, blowjob, cage, crossdressing, cum in mouth, dirty talk, exhibitionist, hd, pornstar, sissy

Pornstars: Tiffany Mynx

aShemaleTube

Dani rides to caged sissygasm clip

Categories: cage, crossdressing, cumshot, hd, lingerie, orgasm, sissy, small cock, solo, toys

KeekAss

Ginormous faux-cock and node for sissy t-girl - Bad Dragon Stan and Bishop

Categories: amateur, anal, anal toying, crossdressing, dick, dildo, hd, huge dildo, masturbation, miniskirt

HDSex

Sex machine, trans, amateur crossdresser

Categories: amateur, anal, crossdressing, dildo, sissy, toys, transsexual

aShemaleTube

Caucasian trap. End

Categories: european, high heels, lingerie, mature, milf, outdoor, pantyhose, sissy, stockings

aShemaleTube

Naughty bitch 2 - Brenna Knight - Kik: brennamason13

Categories: bitch, blowjob, crossdressing, femboy, hd, homevideo, naughty, sissy

aShemaleTube

Fingering and dildo in my femboy ass. Preparing for a big black anal plug and fisting.

Categories: amateur, anal, anal toying, big ass, black, buttplug, crossdressing, dildo, femboy, fingering

aShemaleTube

Sissy pansy Andreina

Categories: barebacking, cage, crossdressing, glasses, hd, high heels, homevideo, lingerie, mature, redhead

KeekAss

Alexa Cosmic t-girl nude on the beach getting muddy with sand and swimming in the river...

Categories: amateur, beach, beauty, blonde, crossdressing, hd, milf, mud, nude, outdoor

aShemaleTube

Dumb anal-crazy sissy slut destroying her boypussy - part 2/3

Categories: amateur, anal, crazy, crossdressing, fetish, fisting, gaping hole, prolapse, sissy, slut

aShemaleTube

Puedes Adivinar? - PMV

Categories: bunny, hd, japanese, sissy, skirt, solo, spanish, striptease

ShemaleMovie

Crossdresser sissy maid endures strict restroom bondage predicament

Categories: amateur, anal, babe, bdsm, beauty, bondage, cage, crossdressing, dildo, gagging

KeekAss

My Very first Ever Dual Sissygasm in Slow Maneuverability

Categories: anal, anal toying, crossdressing, femboy, fishnet, hd, ladyboy, masturbation, sissy, stockings

aShemaleTube

Maid Cosplay

Categories: amateur, cosplay, crossdressing, femboy, maid, masturbation, sissy, solo, teen (18+)

TrannyOne

Sissy Handsfree Orgasmic Compilation

Categories: anal, anus, ass, compilation, crossdressing, cum, desi, hd, orgasm, prostate

aShemaleTube

Spermbutterflies

Categories: 3some, big ass, big cock, crossdressing, femboy, hd, lingerie, pantyhose, sissy, small tits

aShemaleTube

Annemieke Risky Public Fuck

Categories: caught, cute, dick, hd, outdoor, public, sissy

HDSex

Converting my straight roommate into my submissive wife

Categories: amateur, anal, asian, babe, beauty, big cock, brutal, crossdressing, femboy, ladyboy

KeekAss

Sissy Breezy gives me a great Rail - Onlyfans Veronica Sanders

Categories: anal, asian, beauty, big ass, blowjob, booty, brunette, couch, creampie, cum

XXXDan

Hot sissy tied up with a vibrator

Categories: amateur, beauty, bondage, crossdressing, european, fetish, lingerie, sissy, solo, teen (18+)

aShemaleTube

I show my caged clitty on cam blue top rainbow gloves

Categories: amateur, big ass, bimbo, cage, clit, doll, escort, gloves, hd, on top

KeekAss

messy alley bang for XXL jizz facial cumshot sissy change festival

Categories: anal, assfucking, big cock, blowjob, brunette, cumshot, facial, handjob, hd, jizz

aShemaleTube

Blonde taking her bra off in black stockings and lingerie

Categories: amateur, big cock, big tits, black, blonde, bra, crossdressing, femboy, hd, homevideo

VideoSection

Sissys enjoy anal play

Categories: amateur, anal, anal toying, ass, babe, beauty, big ass, big cock, brutal, dildo

KeekAss

bouncy butt fur covered femboy nightly hikes on public trails

Categories: amateur, ass, black, booty, femboy, fur, hd, outdoor, perfect body, public

aShemaleTube

Annemieke playing in front of abandoned restaurant

Categories: crossdressing, dick, flashing, hd, outdoor, public, sissy, solo, stockings

TrannyOne

The secretary heals the boss

Categories: amateur, big cock, blowjob, boss, dick, european, french, hd, ladyboy, lingerie

aShemaleTube

Josydelicia Fetiche Anal Sexy Brinquedo Duro 2025

Categories: amateur, anal, sissy, toys

aShemaleTube

MATURE SISSY PLAYING WITH HER OLD SAGGY COCK

Categories: amateur, crossdressing, dick, hd, lingerie, masturbation, mature, old, pantyhose, saggy tits

aShemaleTube

Sissy Maid Dizzys Day of Bondage

Categories: bdsm, bondage, hd, lingerie, maid, sissy, stockings

TrannyOne

its ok sissy girl by a goddess sissy trainer feminizer

Categories: amateur, crossdressing, gangbang, goddess, homevideo, interracial, sissy, toys

aShemaleTube

Sissy Em Fucked by Master

Categories: amateur, crossdressing, homevideo, master, sissy, stockings

TrannyOne

Tgirl couple fucking anal blowjobs - Tgirlcamz.com free cams

Categories: adorable, amateur, anal, anus, ass, assfucking, babe, bdsm, beauty, big cock

ShemaleMovie

Halloween party, sissy femboy

Categories: cosplay, crossdressing, femboy, halloween, party, sissy

aShemaleTube

3 guys fuck me one by one

Categories: anal, asian, chinese, crossdressing, femboy, group sex, hd, ladyboy, lingerie, model

aShemaleTube

Devine tgirl beauty shows off perfect body 💗💋

Categories: amateur, beauty, femboy, hd, homevideo, latina, lingerie, masturbation, perfect body, sissy

JizzBunker

Sissy Anal Training Session roleplay V0.8 - Intermediate to Expert Ft Sissy Kenzie Star

Categories: anal, big ass, big cock, black, dildo, fetish, huge dildo, lingerie, sissy, slut

KeekAss

Lush Black Sissy Use a Cucumber

Categories: amateur, anal, anal toying, bbw, big ass, black, chubby, crossdressing, cucumber, cum

TrannyOne

My mother's thong cum cover my cum

Categories: amateur, big cock, crossdressing, cum, dick, gay, handjob, hd, lingerie, masturbation

aShemaleTube

Heels up, Legs Open: Foot Fetish Fishnets Cumshot & Sissy

Categories: asian, big cock, crossdressing, cumshot, feet, femboy, fetish, fishnet, hd, high heels

Pornstars: Viper

ShemaleMovie

Plump-booty MILF Andrea Grey mounts Melanie Brooks' shemale cock!

Categories: anal, ass, ass to mouth, babe, beauty, big cock, booty, cowgirl, creampie, dick

KeekAss

Attempting to find the right angle for Opportunity on my pound machine

Categories: anal, asian, big black cock, creampie, cum, femboy, hd, japanese, lingerie, moaning

XXXDan

Sopa enema for sissy MILF slut

Categories: amateur, anal, bdsm, big ass, czech, enema, milf, sissy, slut, solo

aShemaleTube

nice tits American trans milf in glasses webcams solo

Categories: amateur, american, brunette, glasses, homevideo, masturbation, milf, sissy, small cock, small tits

KeekAss

Juggling and Throating with Restrain Bondage and Nip Clips

Categories: amateur, anal toying, bdsm, blonde, bondage, bound, cage, clamp, crossdressing, dildo

ShemaleMovie

Ash-blonde, mask

Categories: blonde, dildo, mask, oral, sissy, toys

aShemaleTube

Hot me skykitty ladyboy shemale facked by Yung boyfriend

Categories: anal, big ass, boyfriend, creampie, crossdressing, femboy, hd, homevideo, ladyboy, sissy

aShemaleTube

Xoangeldolll DildoRide Comp

Categories: anal, big ass, compilation, crossdressing, dildo, femboy, hd, masturbation, sissy, small cock

JizzBunker

Slim and feminine arab sissy with real small tits and big nipples gets fucked in all positions

Categories: amateur, anal, arab, big cock, big nipples, black, blowjob, creampie, crossdressing, gay

XXXDan

Big ass bent over booty ladyboy blonde porn model sissy kitty

Categories: amateur, babysitter, beauty, bend over, big ass, big cock, blonde, booty, college, cosplay